EP0684256A3 - Improved process for the preparation of 3 beta, 14 beta-dihydroxyethialnaldehyde. - Google Patents

Improved process for the preparation of 3 beta, 14 beta-dihydroxyethialnaldehyde. Download PDF

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Publication number
EP0684256A3
EP0684256A3 EP95830069A EP95830069A EP0684256A3 EP 0684256 A3 EP0684256 A3 EP 0684256A3 EP 95830069 A EP95830069 A EP 95830069A EP 95830069 A EP95830069 A EP 95830069A EP 0684256 A3 EP0684256 A3 EP 0684256A3
Authority
EP
European Patent Office
Prior art keywords
beta
dihydroxyethialnaldehyde
preparation
improved process
alkaline periodate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP95830069A
Other languages
German (de)
French (fr)
Other versions
EP0684256A2 (en
EP0684256B1 (en
Inventor
Mauro Gobbini
Marco Torri
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sigma Tau Industrie Farmaceutiche Riunite SpA
Original Assignee
Sigma Tau Industrie Farmaceutiche Riunite SpA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sigma Tau Industrie Farmaceutiche Riunite SpA filed Critical Sigma Tau Industrie Farmaceutiche Riunite SpA
Publication of EP0684256A2 publication Critical patent/EP0684256A2/en
Publication of EP0684256A3 publication Critical patent/EP0684256A3/en
Application granted granted Critical
Publication of EP0684256B1 publication Critical patent/EP0684256B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005—Oxygen-containing hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J15/00—Stereochemically pure steroids containing carbon, hydrogen, halogen or oxygen having a partially or totally inverted skeleton, e.g. retrosteroids, L-isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J19/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 by a lactone ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J3/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J3/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom
    • C07J3/005—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom the carbon atom being part of a carboxylic function
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
    • C07J5/0007—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond not substituted in position 17 alfa
    • C07J5/0015—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond not substituted in position 17 alfa not substituted in position 16

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Fats And Perfumes (AREA)
  • Saccharide Compounds (AREA)
  • Steroid Compounds (AREA)

Abstract

A process for producing 3 beta , 14 beta -dihydroxyethianaldehyde is disclosed wherein the oxidation of the lactone ring of digitoxigenin-3-acetate is conducted with an alkaline periodate in the presence of a catalytic amount of ruthenium tetroxide obtained in situ by reacting RuO2 hydrate or RuCl3 with the alkaline periodate.
EP95830069A 1994-05-26 1995-03-03 Improved process for the preparation of 3 beta, 14 beta-dihydroxyethialnaldehyde Expired - Lifetime EP0684256B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITRM940330A IT1272995B (en) 1994-05-26 1994-05-26 IMPROVED PROCEDURE FOR THE PREPARATION OF 14B-HYDROXY-ETIANALDEHYDE.
ITRM940330 1994-05-26

Publications (3)

Publication Number Publication Date
EP0684256A2 EP0684256A2 (en) 1995-11-29
EP0684256A3 true EP0684256A3 (en) 1996-07-10
EP0684256B1 EP0684256B1 (en) 1998-05-13

Family

ID=11402558

Family Applications (1)

Application Number Title Priority Date Filing Date
EP95830069A Expired - Lifetime EP0684256B1 (en) 1994-05-26 1995-03-03 Improved process for the preparation of 3 beta, 14 beta-dihydroxyethialnaldehyde

Country Status (9)

Country Link
US (1) US5596110A (en)
EP (1) EP0684256B1 (en)
JP (1) JPH07316189A (en)
AT (1) ATE166059T1 (en)
DE (1) DE69502438T2 (en)
DK (1) DK0684256T3 (en)
ES (1) ES2118523T3 (en)
HK (1) HK1009332A1 (en)
IT (1) IT1272995B (en)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5587739A (en) * 1978-12-26 1980-07-02 Mitsui Petrochem Ind Ltd Preparation of aromatic aldehyde or ketone

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5587739A (en) * 1978-12-26 1980-07-02 Mitsui Petrochem Ind Ltd Preparation of aromatic aldehyde or ketone

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
A. MILLS ET AL: "Oxidative Dissolution of Ruthenium Dioxide Dihydrate by Periodate Ions", JOURNAL OF THE CHEMICAL SOCIETY FARADAY TRANSACTIONS., vol. 88, no. 17, 17 September 1992 (1992-09-17), CAMBRIDGE GB, pages 2487 - 2491, XP002001552 *
CHEMICAL ABSTRACTS, vol. 94, no. 13, 30 March 1981, Columbus, Ohio, US; abstract no. 103012, MITSUBISHI PETROCHEMICAL CO LTD.: "Benzaldehyde from Styrene and Analogous Oxidation" page 707; column 2; XP002001553 *
F. X. WEBSTER ET AL: "Synthesis of Diacids and Keto-Acids by Ruthenium Tetraoxide Catalyzed Oxidation of Cyclic Allylic Alcohols and alpha,beta-Unsaturated Ketones", JOURNAL OF ORGANIC CHEMISTRY, vol. 52, no. 4, April 1987 (1987-04-01), EASTON US, pages 689 - 691, XP002001550 *
J. F. TEMPLETON ET AL: "Synthesis of 20-Hydroxy-, 20-Amino-, and 20-Nitro-14-hydroxy-21-nor-5.beta.14.beta.-pregnane C-3 Glycosides and Related Derivatives: Structure Activity Relationships of Pregnanes That Bind to the Digitalis Receptor", JOURNAL OF MEDICINAL CHEMISTRY, vol. 36, no. 1, 8 January 1993 (1993-01-08), WASHINGTON US, pages 42 - 45, XP002001546 *
J. S. BOUTAGY ET AL: "Cardenolide Analogues. I. Route for Preparing Semi-Synthetic Analogues of Digitoxigenin", AUSTRALIAN JOURNAL OF CHEMISTRY, vol. 24, 1971, pages 2723 - 2728, XP002001547 *
LINDIG C ET AL: "Synthese 22-O-substituierter Cardenolide sowie Untersuchungen über den oxidativen Abbau von Cardenoliden mit Kaliumpermanganat", JOURNAL PRAKTISCHE CHEMIE, vol. 328, no. 5-6, 1986, pages 682 - 694, XP002002998 *
R. THOMAS ET AL: "Cardenolide Analogs. V. Cardiotonic Activity of Semisynthetic Analogs of Digitoxigenin", THE JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, vol. 191, no. 2, 1974, pages 219 - 231, XP002001548 *
Y. NAKANO ET AL: "Oxidation of Unsaturated and Hydroxy Fatty Acids by Ruthenium Tetroxide and Ruthenium Oxyanions", JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY, vol. 59, no. 4, April 1982 (1982-04-01), CHAMPAIGN US, pages 163 - 166, XP002001551 *

Also Published As

Publication number Publication date
JPH07316189A (en) 1995-12-05
ATE166059T1 (en) 1998-05-15
DK0684256T3 (en) 1999-01-25
US5596110A (en) 1997-01-21
ITRM940330A0 (en) 1994-05-26
HK1009332A1 (en) 1999-05-28
ES2118523T3 (en) 1998-09-16
DE69502438D1 (en) 1998-06-18
EP0684256A2 (en) 1995-11-29
ITRM940330A1 (en) 1995-11-26
EP0684256B1 (en) 1998-05-13
DE69502438T2 (en) 1998-10-15
IT1272995B (en) 1997-07-01

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